EP1650196A1 - Procede de production de 6,7-bis(2-methoxyethoxy)-quinazolin-4-one - Google Patents

Procede de production de 6,7-bis(2-methoxyethoxy)-quinazolin-4-one Download PDF

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Publication number
EP1650196A1
EP1650196A1 EP04748126A EP04748126A EP1650196A1 EP 1650196 A1 EP1650196 A1 EP 1650196A1 EP 04748126 A EP04748126 A EP 04748126A EP 04748126 A EP04748126 A EP 04748126A EP 1650196 A1 EP1650196 A1 EP 1650196A1
Authority
EP
European Patent Office
Prior art keywords
methoxyethoxy
bis
ethyl
reaction
benzoate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP04748126A
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German (de)
English (en)
Other versions
EP1650196B1 (fr
EP1650196A4 (fr
Inventor
Shigeyoshi Ube Lab. Ube Industries Ltd NISHINO
Kenji c/o Ube Laboratories Ube Ind. Ltd HIROTSU
Hidetaka Ube Laboratories Ube Ind. Ltd. SHIMA
Hiroyuki Ube Lab Ube Industries Ltd. ODA
Shinobu Ube Laboratories Ube Ind. Ltd. SUZUKI
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ube Corp
Original Assignee
Ube Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ube Industries Ltd filed Critical Ube Industries Ltd
Publication of EP1650196A1 publication Critical patent/EP1650196A1/fr
Publication of EP1650196A4 publication Critical patent/EP1650196A4/fr
Application granted granted Critical
Publication of EP1650196B1 publication Critical patent/EP1650196B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/88—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form

Definitions

  • the base is used preferably in an amount of 1.0 to 20 moles, more preferably in an amount of 1.1 to 10 moles, and most preferably in an amount of 1.1 to 5.0 moles based on one mole of ethyl 3,4-dihydroxybenzoate.
  • ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate is obtained.
  • ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate can be isolated or purified for the third step.
  • the isolation or purification can be conducted according to the conventional method such as filtration, concentration, distillation, recrystallization, crystallization, or column chromatography.
  • Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate can also be used in the third step without conducting isolation or purification. In the case that isolation or purification is not conducted, the solvent can be replaced in the third step.
  • the metallic catalyst used in the third step can contain at least one metal atom selected from the group consisting of palladium, platinum and nickel.
  • the metallic catalysts include palladium/carbon, palladium/barium sulfate, palladium hydroxide/carbon, platinum/carbon, platinum sulfide/carbon, palladium-platinum/carbon, platinum oxide and Raney nickel. Palladium/carbon, platinum/carbon, platinum sulfide/carbon and Raney nickel are preferred. The platinum/carbon catalyst is particularly preferred.
  • the metallic catalyst can be used alone or in combination.
  • the final product i.e., ethyl 2-amino-4,5-bis(methoxyethoxy)benzoate
  • the isolation or purification can be conducted according to the conventional method such as filtration, concentration, distillation, recrystallization, crystallization, or column chromatography.
  • Ethyl 2-amino-4,5-bis(methoxyethoxy)benzoate can also be used in the fourth step without conducting the isolation or purification. In the case that the isolation or purification is not conducted, the solvent can be replaced in the fourth step.
  • the ammonium carboxylate is used preferably in an amount of 1.0 to 30 moles, and more preferably in an amount of 1.1 to 10 moles based on one mole of 2-amino-4,5-bis(2-methoxyethoxy)benzoate.
  • the filtrate was concentrated, 3,900 mL of ethyl acetate and 3,900 mL of a saturated aqueous sodium carbonate solution were added to the concentrate.
  • the separated organic layer (ethyl acetate layer) was washed twice with 3,900 mL of a saturated aqueous sodium chloride solution to obtain a solution mixture containing ethyl 3,4-bis(2-methoxyethoxy)benzoate.
  • the solution mixture was analyzed (according to an absolute quantitative method) by a high performance liquid chromatography. It was confirmed that 2,023 g of ethyl 3,4-bis(2-methoxyethoxy)benzoate was produced (reaction yield: 95%).
  • the total yield based on ethyl 3,4-dihydroxybenzoate was 80%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catalysts (AREA)
EP04748126A 2003-07-30 2004-07-30 Procede de production de 6,7-bis(2-methoxyethoxy)-quinazolin-4-one Expired - Lifetime EP1650196B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2003282696 2003-07-30
PCT/JP2004/010965 WO2005012264A1 (fr) 2003-07-30 2004-07-30 Procede de production de 6,7-bis(2-methoxyethoxy)-quinazolin-4-one

Publications (3)

Publication Number Publication Date
EP1650196A1 true EP1650196A1 (fr) 2006-04-26
EP1650196A4 EP1650196A4 (fr) 2007-02-28
EP1650196B1 EP1650196B1 (fr) 2011-03-30

Family

ID=34113782

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04748126A Expired - Lifetime EP1650196B1 (fr) 2003-07-30 2004-07-30 Procede de production de 6,7-bis(2-methoxyethoxy)-quinazolin-4-one

Country Status (8)

Country Link
US (2) US20060276647A1 (fr)
EP (1) EP1650196B1 (fr)
JP (1) JP4569876B2 (fr)
CN (1) CN100540539C (fr)
AT (1) ATE503747T1 (fr)
DE (1) DE602004032028D1 (fr)
ES (1) ES2362734T3 (fr)
WO (1) WO2005012264A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE60328461D1 (de) * 2002-01-28 2009-09-03 Ube Industries Verfahren zur herstellung eines chinazolin-4-onderivats
US7459564B2 (en) 2005-01-13 2008-12-02 Bristol-Myers Squibb Company Substituted biaryl compounds as factor XIa inhibitors
CN101798289B (zh) * 2010-02-08 2012-04-18 天津市炜杰科技有限公司 一种埃罗替尼中间体的制备方法
CN102321033B (zh) * 2011-08-22 2013-10-09 江苏辉丰农化股份有限公司 一种它塞瓦的制备方法
WO2013156835A1 (fr) * 2012-04-16 2013-10-24 Laurus Labs Private Limited Procédé amélioré de préparation d'une forme a de chlorhydrate d'erlotinib
CN102850279A (zh) * 2012-10-10 2013-01-02 山东金城医药化工股份有限公司 6,7-二(2-甲氧基乙氧基)喹唑啉-4-酮的制备方法
CN104725327B (zh) * 2015-03-03 2017-08-25 山东大学 一种盐酸厄洛替尼的环保制备方法
CN106892821B (zh) * 2015-12-21 2021-06-11 浙江九洲药业股份有限公司 一种3,4-二(2-甲氧基乙氧基)苯甲酸乙酯的制备方法
CN105566233B (zh) * 2015-12-31 2018-08-17 重庆威鹏药业有限公司 厄洛替尼中间体的制备方法
CN106928069B (zh) * 2017-03-21 2019-03-19 上海玉函化工有限公司 一种4,5-二(2-甲氧基乙氧基)-2-硝基苯甲酸乙酯的制备方法
CN108358798A (zh) * 2018-02-12 2018-08-03 黑龙江鑫创生物科技开发有限公司 一种微通道反应器合成厄洛替尼中间体的方法
CN113603650B (zh) * 2021-08-03 2023-03-10 杭州职业技术学院 一种埃罗替尼关键中间体的催化环合制备方法及其应用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002016360A2 (fr) * 2000-08-18 2002-02-28 Cor Therapeutics, Inc. Composes heterocycliques azotes

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3119824A (en) * 1964-01-28 L-substituted-l
US4096144A (en) * 1970-12-08 1978-06-20 Sumitomo Chemical Company, Limited Process for preparing quinazolinone derivatives and their 2-(N-mono-substituted amino)-phenyl ketone intermediate derivatives
JPS63126867A (ja) * 1986-11-14 1988-05-30 Mitsui Petrochem Ind Ltd イミダゾ−ル誘導体の製法
JPH0629234B2 (ja) * 1986-12-26 1994-04-20 三井石油化学工業株式会社 α−アシロキシケトン誘導体
PT100905A (pt) * 1991-09-30 1994-02-28 Eisai Co Ltd Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem
US5747498A (en) 1996-05-28 1998-05-05 Pfizer Inc. Alkynyl and azido-substituted 4-anilinoquinazolines
JP2002293773A (ja) 2001-03-30 2002-10-09 Sumika Fine Chemicals Co Ltd キナゾリン誘導体の製造方法
WO2003000188A2 (fr) 2001-06-21 2003-01-03 Ariad Pharmaceuticals, Inc. Nouvelles quinazolines et leur utilisation
WO2003051849A1 (fr) * 2001-12-19 2003-06-26 Ube Industries, Ltd. Procede de production de quinazoline-4-one et derive de celle-ci
DE60328461D1 (de) * 2002-01-28 2009-09-03 Ube Industries Verfahren zur herstellung eines chinazolin-4-onderivats
DE10204150A1 (de) 2002-02-01 2003-08-14 Schott Glas Erdalkalialuminosilicatglas und Verwendung

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002016360A2 (fr) * 2000-08-18 2002-02-28 Cor Therapeutics, Inc. Composes heterocycliques azotes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2005012264A1 *

Also Published As

Publication number Publication date
EP1650196B1 (fr) 2011-03-30
ES2362734T3 (es) 2011-07-12
WO2005012264A1 (fr) 2005-02-10
CN100540539C (zh) 2009-09-16
EP1650196A4 (fr) 2007-02-28
JPWO2005012264A1 (ja) 2007-09-27
US8133999B2 (en) 2012-03-13
US20060276647A1 (en) 2006-12-07
ATE503747T1 (de) 2011-04-15
CN1860105A (zh) 2006-11-08
DE602004032028D1 (de) 2011-05-12
JP4569876B2 (ja) 2010-10-27
US20090253909A1 (en) 2009-10-08

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